29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy travel route planner

Make it your trip
Drive to Washington Dulles International Airport, Fly to Malpensa International Airport
1
Milan
— 2 nights
Drive
2
Varenna
— 3 nights
Drive
3
Cinque Terre
— 3 nights
Drive
4
Florence
— 5 nights
Train
5
Bologna
— 3 nights
Fly
6
Salerno
— 3 nights
Drive
7
Sorrento
— 3 nights
Train
8
Rome
— 5 nights
Fly to Washington Dulles International Airport, Drive to Dulles

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Milan

— 2 nights

Fashion Capital of World

In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Kick off your visit on the 28th (Tue): contemplate in the serene atmosphere at Duomo di Milano, then don't miss a visit to Piazza del Duomo, then explore the historical opulence of Castello Sforzesco, and finally admire the landmark architecture of Galleria Vittorio Emanuele II.

Before you visit Milan, use our trip planner to discover what you can do and see there.

Dulles, USA to Milan is an approximately 17.5-hour combination of car and flight. You can also do a combination of car and flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. September in Milan sees daily highs of 76°F and lows of 57°F at night. Wrap up your sightseeing on the 29th (Wed) early enough to drive to Varenna.

Things to do in Milan

Historic Sites · Shopping
Find places to stay Sep 27 — 29:

Varenna

— 3 nights
Varenna is a comune (municipality) on Lake Como in the Province of Lecco in the Italian region Lombardy, located about 60km north of Milan and about 20km northwest of Lecco.Varenna was founded by local fishermen in 769, and was later allied of the commune of Milan. Change things up with these side-trips from Varenna: Tremezzina (Villa Carlotta & Villa del Balbianello), Bellagio (Basilica di San Giacomo & I Giardini di Villa Melzi) and The Anglican Church of the Ascension (in Cadenabbia di Griante). And it doesn't end there: step into the grandiose world of Castello di Vezio, stop by Il Tornio, explore the stunning scenery at Orrido di Bellano, and pause for some serene contemplation at Chiesa di San Giorgio.

For where to stay, more things to do, other places to visit, and more tourist information, read Varenna trip itinerary maker site.

Getting from Milan to Varenna by car takes about 1.5 hours. Expect a daytime high around 76°F in September, and nighttime lows around 57°F. Finish your sightseeing early on the 2nd (Sat) so you can drive to Cinque Terre.

Things to do in Varenna

Parks · Nature · Museums · Historic Sites

Side Trips

Find places to stay Sep 28 — Oct 2:

Cinque Terre

— 3 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Change things up with these side-trips from Cinque Terre: Parco Naturale Regionale di Porto Venere (in La Spezia), Porto Venere (Grotta di Byron & Portovenere) and Genoa (Piazza Raffaele De Ferrari, Boccadasse, &more). There's still lots to do: discover the deep blue sea with Enjoy Cinqueterre Boat Tours, don't miss a visit to Oratorio della Confraternita dei Neri Mortis et Orationis, hike along Cinque Terre Trails, and stroll through Footpath Monterosso - Vernazza.

For photos, traveler tips, maps, and other tourist information, read our Cinque Terre travel route tool.

Traveling by car from Varenna to Cinque Terre takes 4 hours. Alternatively, you can take a train. Expect a bit warmer weather when traveling from Varenna in October: highs in Cinque Terre hover around 71°F, while lows dip to 54°F. Wrap up your sightseeing on the 5th (Tue) early enough to drive to Florence.

Things to do in Cinque Terre

Parks · Outdoors · Neighborhoods · Trails

Side Trips

Find places to stay Oct 2 — 5:

Florence

— 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Change things up with these side-trips from Florence: Castello del Trebbio (in Santa Brigida) and Pisa (Museo Aviotruppe Esercito Italiano, Leaning Tower of Pisa, &more). There's still lots to do: don't miss a visit to Piazzale Michelangelo, explore the world behind art at Pitti Palace, take in nature's colorful creations at The Boboli Gardens, and get to know the fascinating history of Piazza del Duomo.

For traveler tips, reviews, more things to do, and tourist information, you can read our Florence trip planner.

Drive from Cinque Terre to Florence in 2.5 hours. Alternatively, you can take a train. In October in Florence, expect temperatures between 71°F during the day and 54°F at night. Wrap up your sightseeing on the 10th (Sun) to allow time to take a train to Bologna.

Things to do in Florence

Historic Sites · Museums · Tours · Wineries

Side Trips

Find places to stay Oct 5 — 10:

Bologna

— 3 nights

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Kick off your visit on the 11th (Mon): take in the architecture and atmosphere at Santuario di Madonna di San Luca, contemplate the long history of Piazza Santo Stefano, enjoy breathtaking views from Le Due Torri Torre degli Asinell, then see the interesting displays at La Macchina del Tempo, then take in the architecture and atmosphere at Basilica - Santuario di Santo Stefano, and finally admire the landmark architecture of Palazzo Magnani. Get ready for a full day of sightseeing on the next day: steep yourself in history at Piazza Maggiore, get engrossed in the history at Museo Civico Medievale, then explore the historical opulence of Castello Estense, then contemplate the long history of Palazzo Schifanoia (Palazzo della Gioia), and finally pick up a one of a kind souvenir at Libreria Belriguardo.

To find other places to visit, where to stay, more things to do, and other tourist information, read our Bologna travel route planner.

You can take a train from Florence to Bologna in 1.5 hours. Other options are to drive; or take a bus. Expect a daytime high around 67°F in October, and nighttime lows around 52°F. Cap off your sightseeing on the 13th (Wed) early enough to travel to Salerno.

Things to do in Bologna

Historic Sites · Museums · Shopping

Side Trip

Find places to stay Oct 10 — 13:

Salerno

— 3 nights

Unspoilt Gem of the Amalfi Coast

While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
Change things up with these side-trips from Salerno: Ravello (Ceramiche Cosmolena di Margherita di Palma, Villa Cimbrone Gardens, &more) and Amalfi (Cloister del Paradiso, Duomo di Sant'Andrea, &more). And it doesn't end there: delve into the distant past at Pompeii Archaeological Park, cruise along Amalfi Coast, take an in-depth tour of Museo Archeologico Provinciale di Salerno, and make a trip to Medieval Aqueduct.

To find traveler tips, reviews, photos, and other tourist information, read our Salerno journey planner.

Getting from Bologna to Salerno by flight takes about 4.5 hours. Other options: take a train; or drive. Traveling from Bologna in October, expect Salerno to be somewhat warmer, temps between 73°F and 63°F. Finish your sightseeing early on the 16th (Sat) to allow enough time to drive to Sorrento.

Things to do in Salerno

Historic Sites · Parks · Museums · Outdoors

Side Trips

Find places to stay Oct 13 — 16:

Sorrento

— 3 nights

Land of the Sirens

A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Venture out of the city with trips to Torre di Grado (in Praiano) and Positano (Boat Tours & Water Sports & Il Sentiero Degli Dei). Dedicate the 18th (Mon) to wine at some of the top wineries in the area. And it doesn't end there: indulge in some culinary diversions at a local gastronomic tour, contemplate in the serene atmosphere at St Francis Church and Convent, take in the waterfront at Marina Grande - Antico Borgo Marinaro, and admire the striking features of Basilica di Sant'Antonino.

For ratings, traveler tips, reviews, and tourist information, go to the Sorrento road trip planner.

You can drive from Salerno to Sorrento in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and subway. In October, daily temperatures in Sorrento can reach 72°F, while at night they dip to 63°F. Wrap up your sightseeing on the 19th (Tue) early enough to take a train to Rome.

Things to do in Sorrento

Tours · Wineries · Historic Sites · Outdoors

Side Trips

Find places to stay Oct 16 — 19:

Rome

— 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: contemplate the long history of Colosseum, explore the world behind art at Galleria Borghese, don't miss a visit to Roman Forum, and admire the local landmark of Trevi Fountain.

To see where to stay, more things to do, maps, and more tourist information, you can read our Rome travel route planning app.

Traveling by train from Sorrento to Rome takes 3 hours. Alternatively, you can drive; or take a bus. Plan for slightly colder nights when traveling from Sorrento in October since evenings lows in Rome dip to 55°F. You will have some time to spend on the 24th (Sun) before leaving for home.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trip

Find places to stay Oct 19 — 24:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.